115698-64-1

Upstream product

• 122937-62-6 (Z)-(R)-4-(2-Bromo-1-ethoxy-ethoxymethyl)-hex-2-enoic acid methyl ester 
• 111042-76-3 (-)-(2S)-2-((tert-Butyldimethylsiloxy)methyl)butan-1-ol 
• 188434-50-6 (4R,5R)-2-ethoxy-5-ethyl-4-<(methoxycarbonyl)methyl>-3,4,5,6-tetrahydro-2H-pyran 
• 131815-06-0 [(S)-2-(2-Bromo-1-ethoxy-ethoxymethyl)-butoxy]-tert-butyl-dimethyl-silane 
• 122937-61-5 (R)-2-(2-Bromo-1-ethoxy-ethoxymethyl)-butan-1-ol 
• 131815-04-8 (S)-2-(2-Bromo-1-ethoxy-ethoxymethyl)-butyraldehyde 
• 131815-09-3 2-((4S,5R)-2-Ethoxy-5-ethyl-tetrahydro-pyran-4-yl)-ethanol 
• 100-39-0 benzyl bromide 
• 122778-44-3 (1R,3R,4S)-p-menthan-3-yl (2R)-2-(dimethyl-t-butylsiloxymethyl)butyrate 
• 122937-62-6 (-)-Methyl (4R)-(Z)-4-(2-Bromo-1-ethoxyethoxymethyl)hex-2-enoate 
• 122937-63-7 (-)-(4R,5R)-2-Ethoxy-5-ethyl-4-methoxycarbonylmethyl-3,4,5,6-tetrahydro-2H-pyran 
• 122937-61-5 (+)-(2R)-(2-Bromo-1-ethoxyethoxymethyl)butan-1-ol 
• 601-75-2 ethylmalonic acid 
• 122937-59-1 (+)-(1S,3S,4R)-p-Menthan-3-yl (2S)-2-(t-Butyldimethylsiloxymethyl)butyrate 

Downstream Products

• 122937-64-8 (+)-(3S,4R)-3-(2-Benzyloxyethyl)-N-(3,4-dimethoxyphenethyl)-4-hydroxymethylhexacarboxamide 
• 123001-22-9 (4R,5R)-4-(2-Benzyloxyethyl)-5-ethyl-3,4,5,6-tetrahydro-2-pyrone 
• 123001-21-8 (+)-(4S,5R)-4-(2-Benzyloxyethyl)-5-ethyl-3,4,5,6-tetrahydro-2-pyrone 
• 122937-65-9 (-)-(2R,3R,11bS)-2-(2-Benzyloxyethyl)-3-ethyl-1,2,3,4,6,7-hexahydro-9,10-dimethoxy-11bH-benzoquinolizidine 
• 115698-60-7 (4S,5R)-4-(2-Benzyloxy-ethyl)-5-ethyl-tetrahydro-pyran-2-ol 

Relevant academic research and scientific papers

Asymmetric Total Synthesis of (-)-Protoemetinol, (-)-Protoemetine, (-)-Emetine, and (-)-Tubulosine by Highly Stereocontrolled Radical Cyclisations

Both enantiomers of the menthyl half-esters (10) and (23) of ethylmalonic acid were converted into (+)-(4S,5R)-4-(2-benzyloxyethyl)-5-ethyl-3,4,5,6-tetrahydro-2-pyrone (18).A mixture of the trans-(18) and cis-lactones (19) in a ratio of ca. 4:1 was prepared by way of radical cyclisation of the (E)-α,β-unsaturated esters (16), while the former (18) was synthesised with high stereoselection by the cyclisation of the (Z)-esters (26).The lactone (18) was enantioselectively transformed into (-)-protoemetinol (5) and (-)-protoemetine (4), correlated to (-)-emetine (1) and (-)-tubulosine (3).

HIGHLY ENANTIOCONTROLLED TOTAL SYNTHESYS OF (-)-PROTOEMETINOL

Enantiomerically pure (-)-protoemetinol (1) was selectively synthesized from ethylmalonic acid via radical cyclization of the (Z)-α,β-unsaturated ester (12).